SEC Form 4
Washington, D.C. 20549


Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940
OMB Number: 3235-0287
Estimated average burden
hours per response: 0.5
Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).
1. Name and Address of Reporting Person*

(Last) (First) (Middle)


(City) (State) (Zip)
2. Issuer Name and Ticker or Trading Symbol
Upland Software, Inc. [ UPLD ]
5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)
X Director 10% Owner
X Officer (give title below) Other (specify below)
3. Date of Earliest Transaction (Month/Day/Year)
4. If Amendment, Date of Original Filed (Month/Day/Year)
6. Individual or Joint/Group Filing (Check Applicable Line)
X Form filed by One Reporting Person
Form filed by More than One Reporting Person
Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3) 2. Transaction Date (Month/Day/Year) 2A. Deemed Execution Date, if any (Month/Day/Year) 3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4)
Code V Amount (A) or (D) Price
Common Stock 01/12/2022 A 93,750(1) A $0 1,511,966(2) D
Common Stock 153,738 I By National Financial Services as Cust FBO J. McDonald RRA
Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned
(e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (Month/Day/Year) 3A. Deemed Execution Date, if any (Month/Day/Year) 4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 6. Date Exercisable and Expiration Date (Month/Day/Year) 7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4)
Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares
Performance Share Unit $0.0 (3) (3) Common Stock 61,437 61,437 D
Performance Share Unit $0.0 01/12/2022 A 93,750(4) (4) 06/18/2023 Common Stock 93,750 $0 93,750 D
Explanation of Responses:
1. Represents restricted stock units vesting in twelve equal quarterly installments starting on March 16, 2022 and ending on December 16, 2024; provided that the participant continues to be a service provider through each such vesting date.
2. Does not include 125,000 shares of common stock held in a trust for the benefit of Mr. McDonald's children of which The Bryn Mawr Trust Company of Delaware is the trustee.
3. 0% to 300% of these TSR performance PSUs may vest on June 30, 2022 based on the Company's total stockholder return ("TSR") for the 18 month period ending June 30, 2022. The percentage of TSR Performance PSUs that may vest will be (a) 0% if TSR is below 5.0%; (b) 50% if TSR is 5.0%; (c) 100% if TSR is 10%; and (d) 300% if TSR is 20% or greater. If TSR is between 5.0% and 10% or between 10% and 20%, the percentage of TSR Performance RSUs that may vest is determined using linear interpolation.
4. Units will vest on the first date on which the closing price of Upland's common stock for any thirty (30) consecutive trading days immediately preceding such date before June 30, 2023 equals or exceeds certain stock price hurdles. On June 30, 2023, a number of Units (if any) will vest based on the closing price of Upland's common stock on June 30, 2023 using linear interpolation. Total shares earned will be between 0% and 300% of the target number of shares reported.
/s/ Kin Gill (as attorney-in-fact for Mr. McDonald) 01/14/2022
** Signature of Reporting Person Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.